Ethylene Oxide → 3-Benzenesulfonyl-3-methyl-butan-1-ol

HRID 2212069Notes

Reaction equation

C([Li])CCC.[C:6]1([S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:18]1[O:20][CH2:19]1>O1CCCC1>[C:6]1([S:12]([C:15]([CH3:17])([CH3:16])[CH2:19][CH2:18][OH:20])(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: -40 °C

Procedure

A solution of n-butyllithium in cyclohexanes (1.8M, 35.1 ml; 63.18 mmol) was added dropwise to a stirred solution of isopropyl phenyl sulphone (9.95 g, 54 mmol) in tetrahydrofuran (100 ml) keeping the temperature of the mixture below −60° C. The mixture was stirred for 30 min. and ethylene oxide was passed through the reaction mixture for 10 min. The mixture was warmed up to −40° C. for 30 min., then quenched with sat. aqueous NH4Cl and extracted into ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified on silica gel (i-hexane:ethyl acetate) to give the title compound (12.3 g, 99%).

Workup

customthe temperature of the mixture below −60° C
customquenched with sat. aqueous NH4Cl
extractionextracted into ethyl acetate
dry with materialThe combined organic extracts were dried (Na2SO4)
concentrationconcentrated
customThe residue was purified on silica gel (i-hexane:ethyl acetate)

Sources & evidence

ORD record: ord-f8737e092ee344178f600929b7151bbd
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101892B2

Reaction notes

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